Quantitative Structure-Activity Relationships of Antifungal 1-[1-(Substituted phenyl)vinyl]imidazoles

隆博, 片岡; 浩幸, 甲斐; 一郎, 石塚; 隆行, 八田; 秀, 尾形

doi:10.1584/jpestics.12.445

Cited by 4 publications

(4 citation statements)

References 2 publications

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“…The correlations represented by Eqs. (4) and (5) are excellent and the slopes of the corresponding terms and intercepts are almost identical between the two equations. The coefficient of Isat in Eq.…”

Section: Qsar Of 1-[2-(2-substituted Hydroxy-5-mentioning

confidence: 82%

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Synthesis and Quantitative Structure-Activity Relationships of New Antifungal 1-[2-(Substituted phenyl) allyl] imidazoles and Related Compounds

1988

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A number of 1-[2-(2-substituted hydroxy-5-substituted phenyl)allyl]imidazole derivatives and their related compounds were newly synthesized. The allylimidazoles showed a potent activity in vitro against Botrytis cineyea, a phytopathogenic fungus. The relationship between structure and activity was examined quantitatively using physicochemical and structural parameters and regression analysis. Hydrophobicity of the molecule was the most important factor for the activity. The activity increased as the hydrophobicity increased and bulkiness of a substituent at the 5-position on the benzene ring decreased. Unsubstitution at the 5position on the benzene ring did not favor the activity, however. Conversion of a double bond of the allyl moiety to a single bond deteriorated the activity. The present series of allylimidazoles was higher in activity than the previous series of the corresponding 1-[1-(2-substituted hydroxy-5-substituted phenyl)vinyl]imidazoles, which has been reported.

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Section: Qsar Of 1-[2-(2-substituted Hydroxy-5-mentioning

confidence: 82%

“…(2), and the slopes of the corresponding terms and intercepts are almost identical between Eqs. (3) and (4). Table 7 shows that the internal correlation among independent variables in Eq.…”

Section: Qsar Of 1-[2-(2-substituted Hydroxy-5-mentioning

confidence: 99%

Synthesis and Quantitative Structure-Activity Relationships of New Antifungal 1-[2-(Substituted phenyl) allyl] imidazoles and Related Compounds

1988

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“…55-0.67. 4,5) The relationship between the curative and in vitro activities of vinylimidazoles I and the relationship between those of allylimidazoles II were combined by Eq. (6).…”

Section: ) Eqs (8) and (6)mentioning

confidence: 99%

“…Quantitative structure-activity relationships showed that molecular hydrophobicity as well as certain submolecular steric and structural factors is important in determining variations in the antif ungal potency. 4,5) More recently, we have measured their protective and curative antif ungal activities against B. cinerea under greenhouse conditions. This paper reports the relationships between the antifungal activities of vinylimidazoles I and allylimidazoles II in greenhouse and in vitro conditions with the aid of physicochemical and structural parameters and regression analysis.…”

Section: Introductionmentioning

confidence: 99%

Relationship between Antifungal Activities in Greenhouse and <i>in Vitro</i> of 1-[1-(Substituted phenyl)vinyl]imidazoles and 1-[2-(Substituted phenyl)allyl]imidazoles

et al. 1988

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Protective and curative antifungal activities of 16 1-[1-(2-substituted hydroxy-5-substituted phenyl)vinyl]imidazoles and 9 1-[2-(2-substituted hydroxy-5-substituted phenyl)-allyl]imidazoles were measured against Botrytis cinerea, a phytopathogenic fungus, under greenhouse conditions. A relationship between their antifungal activity in greenhouse conditions and that in vitro was examined quantitatively based on the regression analysis with the aid of physicochemical and structural parameters. The higher the in vitro activity, the higher the protective activity in greenhouse conditions. The protective activity was more persistent in the vinylimidazoles than in the corresponding allylimidazoles. The curative activity in greenhouse conditions increased as the activity in vitro increased. Substitution of the 2, 6-dichlorobenzyloxy group at the 2-position on the benzene ring was favorable to the curative activity. The curative activity does not seem to depend on the hydrophobicity of the molecule, because the positive effect of the log P term on the in vitro activity and the negative effect on the mobility within the leaf cancel each other.

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The hypothetical active site lattice ? in vitro and in vivo explorations using a three-dimensional QSAR technique

Doweyko¹

1991

J Math Chem

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Quantitative Structure-Activity Relationships of Antifungal 1-[1-(Substituted phenyl)vinyl]imidazoles

Cited by 4 publications

References 2 publications

Synthesis and Quantitative Structure-Activity Relationships of New Antifungal 1-[2-(Substituted phenyl) allyl] imidazoles and Related Compounds

Synthesis and Quantitative Structure-Activity Relationships of New Antifungal 1-[2-(Substituted phenyl) allyl] imidazoles and Related Compounds

Relationship between Antifungal Activities in Greenhouse and <i>in Vitro</i> of 1-[1-(Substituted phenyl)vinyl]imidazoles and 1-[2-(Substituted phenyl)allyl]imidazoles

The hypothetical active site lattice ? in vitro and in vivo explorations using a three-dimensional QSAR technique

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